Tuscany itinerary for 5 days: how to plan and which towns to visit

September 8, 2015

It was Easter and since we have a direct flight from Copenhagen to Pisa, what a better way to spend the holiday than to go to Tuscany for 6 days.

This part of Europe is stunning; you have the wooded mountains in the north Tuscany and the rolling hills covered with vineyards, endless olive groves and cypress trees in the south, considered by many a typical Tuscan scene. Wherever you decide to go, I’m sure you won’t be disappointed.

For our six-day trip, we decided on an itinerary that would cover a little bit of everything.

This is our Tuscany itinerary, so you can have an idea:

Tuscany itinerary

Like in most of our short trips, hiring a car is a must. It gives you the freedom and flexibility to stop anywhere on the road as well as covering many destinations. Usually for our rentals in Europe we use either http://www.rentalcars.com/ or https://www.locationdevoiture.fr/. In case your credit card doesn’t cover your insurance for the car, locationdevoiture has a much better price, fully covered.

If you plan on visiting only the major cities like Pisa, Luca, Florence, and Siena than you most probably don’t need a car since trains in Italy are quite fast and reliable. We dropped our car off in Florence and took the train to Rome, for instance; it made more sense like this. Being the most important religious holiday in Italy we booked the ticket online a few weeks in advance. It covers the distance of 300 km in 1,5 hours (average speed of 250kms/h), which for 20e p/p is pretty good.

This is our 6 day itinerary that will take you through the most breathtaking sights of beautiful Tuscany:

Day 1: Visit Pisa, Luca and San Gimignano

Since our plane landed in Pisa early in the morning, we opted to pick-up our rental from the city rather than the airport, giving us the opportunity to explore Pisa without worrying about parking.

This is Piazza dei Miracoli and its famous leaning tour, the marvelous piece of architecture gone wrong, and the iconic landmark of Pisa.

That’s where you need to go

Nice to have such a background

Pisa Baptistery of St. John

The Leaning Tower of Pisa

Duomo di Pisa

Only 18 km north you’ll find the small medieval town of Lucca.

Amphitheatre Square in Lucca

The Church of San Michele in Lucca

Driving SE from Lucca you’ll reach San Gimignano in about an hour and a half. Just park the car in the cheaper P1 GIUBILEO and go explore this beautiful typical Tuscany town.

An alley in San Gimignano

Piazza del Duomo in San Gimignano

The towers of San Gimignano

San Gimignano is widely known as the City of the Beautiful Towers—and it’s easy to see why. Try to avoid the crowded main street and just stroll the lovely small parallel streets. The town is one of the best-preserved examples of medieval architecture and the weird looking towers just fit perfectly. The time seems to have stopped a few hundred years ago for this little town.

Day 2&3: Monteriggioni, Siena, Montepulciano

We spent the night at the wonderful Villa Gloria. Here is the view from our balcony.

Tuscany landscape

Villa-Gloria

We hit the road soon after breakfast wanting to maximize our time in Siena. On the way though, you could “sacrifice” half an hour to visit the very small town (only about 55 inhabitants) of Monteriggioni. Everyone who ever played the Assassin’s Creed II will find familiar sites here, especially the surrounding wall, not to mention that even Dante compares the turrets of Monteriggioni to the giants surrounding the abyss in His Divine Comedy.

Monteriggioni

Monteriggioni

Siena is a jewel of Tuscany. Climb the Torre di Mangia for a breathtaking view of the city. The Duomo has a great architecture and inside you’ll find works by Donatello, Bernini, Michelangelo, and Pisano. The floor and the ceiling are also covered in art.

Piazza Del Campo Palazzo Pubblico Siena

Panoramic view over Piazza del Campo Siena

Inside the Cathedral in Siena

Ceiling artwork inside the Dome

We bought an Opa Si Pass, a combined ticket which gives you access to 6 touristic objectives for just 12E. However, be prepared to wait in huge queues to enter any objective. You wait in long lines even to get the tickets. At least that was the case when we were there, around Easter.

Before finding our accommodation, we stopped for a quick evening visit at Montelpuciano.

Montepulciano panoramic view

Beautiful small alley in Montepulciano

Montepulciano Central Square

For our third night, we chose a very typical Tuscan Agriturismo, Il Macchione; an 18th-century stone farmhouse just 1.6 km outside Pienza. Too bad it wasn’t warm enough to test the pool. We highly recommend this place.

Day 4: Castellina, Panzano, Florence

We left early morning, after a great breakfast, having a long road ahead towards Florence.

On the way, we stopped at two little towns: Castellina and Panzano

Church of San Salvatore Castellina Chianti

Fortress in Castellina

Panzano Chianti

Santa Maria Church in Panzano

Once in Florence, we got rid of the car, found our hotel and realized we still had a few good hours left to explore the city.

Florence is a small jewel box: totally walkable and charming. Amazing art, architecture, churches but that is no surprise since the Renaissance was born here.

View over Florence

Neptune Fountain in Piazza Della Signora

Palazzio Vecchio

The ideal time allocation for a city like Firenze would be 3 days. Unfortunately on this occasion, we only had a little over one full day. It wasn’t enough but we did manage to see the top attractions, considering we have some experience in planning and having a coffee is a 2 minutes job. Italians drink their very short and flavorful espresso standing.

But if you do have 3 days, a Firenze Card, at 72E for 72hrs would probably be a good idea.

On this trip, we didn’t have time for any museums. From what I’ve learned, most museums are displaying the art of a religious nature but if we were to visit one, it would have been Palacio Pitti for its diversity of paintings.

Palazzo Pitti

Probably my least favorite part of Florence is the Ponte Vecchio, the city’s famous medieval arched bridge. It’s nice from the distance, but totally packed when you’re on it. The jewelry stores are one next to the other and they mostly sell overpriced and gaudy jewelry, a typical tourist trap.

Ponte Vecchio

Day 5: Florence and the afternoon train to Rome

And what is a trip to Tuscany without some of its culinary symbols:

Food shop

Mmmm…gelato

Italian coffee

Day 6, 7, 8: Rome and the Vatican

This is a roughly 350 km itinerary. It may seem a bit crowded but the towns are really small and not so far apart. We felt comfortable like this, but you can skip towns and do it at your own pace.